JP6971316B2 - Organic electroluminescent compounds and organic electroluminescent devices containing them - Google Patents

Description

The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices comprising them.

An electroluminescent device (EL device) is a self-luminous device that has the advantage of providing a wider viewing angle, a larger contrast ratio and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 by using a small aromatic diamine molecule and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Let. 51,913,1987].

The most important factor in determining the luminous efficiency of an organic electroluminescent device is the luminous material. To date, fluorescent materials have been widely used as light emitting materials. However, in consideration of the electroluminescent mechanism, the phosphorescent light emitting material has been widely studied for the development of the phosphorescent light emitting material because the luminous efficiency is theoretically increased by 4 times as much as that of the fluorescent light emitting material. To date, bis (2- (2'-benzothienyl) -pyridinato-N, C3') iridium (acetylacetoneate) ((acac) Ir (btp) ₂ ), tris (2- (2'-benzothienyl) -pyridinato-N, C3') as red, green and blue materials, respectively. 2-Phenylpyridine) Iridium (III) complexes, such as iridium (Ir (ppy) ₃ ) and bis (4,6-difluorophenylpyridinato-N, C2) picolinate iridium (Firpic), are widely known as phosphorescent materials. Has been done.

Currently, 4,4'-N, N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. Recently, Pioneer (Japan) et al. Have used bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq) as host materials as hole blocking layer materials. ) Etc. have been developed for high-performance organic electroluminescent devices.

Although these materials provide good emission properties, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their decomposition is high temperature deposition in vacuum. It can occur during the process and shortens the life of the device. (2) The power efficiency of an organic electroluminescent device is given by [(π / voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Organic electroluminescent devices containing phosphorescent host materials provide higher current efficiency (cd / A) than those containing fluorescent materials, but require a significantly higher drive voltage. Therefore, there is no merit from the viewpoint of power efficiency (lm / W). (3) Further, when these materials are used in an organic electroluminescent device, the operating life of the organic electroluminescent device needs to be short and the luminous efficiency still needs to be improved.

In addition, the electron transport material actively transports electrons from the cathode to the light emitting layer, suppresses the transport of holes that do not recombine in the light emitting layer, and provides an opportunity for recombination of holes and electrons in the light emitting layer. Increase. Therefore, the electron affinity material is used as the electron transport material. Organometallic complexes having a light emitting function such as Alq ₃ are excellent in transporting electrons and have therefore been conventionally used as an electron transporting material. However, Alq ₃ has the problem in that it moves to other layers and exhibits reduced color purity when used in blue light emitting devices. Therefore, there is a need for a novel electron transport material that does not have the above-mentioned problems, has extremely electron affinity, and rapidly transports electrons in the organic EL device to provide an organic EL device having high luminous efficiency. ..

Various materials or concepts have been proposed for the organic layer of organic electroluminescent devices to improve luminous efficiency, drive voltage and / or lifetime. However, they were not satisfactory for practical use.

Korean Patent Application Publication No. 2016-0034804A discloses a compound in which a substituted triazinyl group or a pyrimidinyl group is bound to benzocarbazole by a linker of a biphenylene group at the nitrogen position. However, the above-mentioned reference does not specifically disclose a compound in which a substituted triazinyl group, a pyrimidinyl group, or the like is bonded to benzocarbazole by a linker of an arylene group having 10 carbon atoms at the nitrogen position. Moreover, it is not fully satisfactory in terms of drive voltage, luminous efficiency and / or lifetime characteristics.

It is an object of the present disclosure to provide an organic electroluminescent compound capable of efficiently producing an organic electroluminescent device having low drive voltage, high luminous efficiency and / or excellent lifetime characteristics.

As a result of the invention research for solving the above technical problem, the present inventors have stated that the above object is the following formula 1:

(During the ceremony,
X _{1 to} X ₃ each independently represent _{N or CR 3} provided that at least one of them is N;
L ₁ represents a substituted or unsubstituted arylene having 10 carbon atoms;
Ar ₁ , Ar ₂ and R _{1 to} R ₃ are independently hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted, respectively. Alternatively, unsubstituted (3 to 30-membered ring) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted. Alternatively, unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted. Alternatively, unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino. A substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic ring, aromatic ring or a combination thereof, wherein the carbon atom thereof is represented by a substituted or unsubstituted monocyclic or polycyclic ring, aromatic ring, or a combination thereof. Forming substituted or unsubstituted monocyclic or polycyclic (C3-C30) aliphatic rings, aromatic rings or combinations thereof that can be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur;
Heteroaryl contains at least one heteroatom selected from B, N, O, S, Si and P;
a is an integer of 1 to 4, and b is an integer of 1 to 6;
Where a or b is an integer greater than or _{equal to 2} , and each R ₁ and each R 2 may be the same or different).
We have found that this can be achieved with the organic electroluminescent compounds represented by.

Advantageous Effects of the Invention By using the organic electroluminescent compounds according to the present disclosure, organic electroluminescent devices having low drive voltage, high luminous efficiency and / or excellent life characteristics can be produced.

The disclosure is described in detail below. However, the following statements are intended to illustrate this disclosure and by no means limit the scope of this disclosure.

The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and may optionally be included in any layer constituting the organic electroluminescent device.

The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and may include at least one compound. The organic electroluminescent material may optionally be included in any layer constituting the organic electroluminescent device. For example, organic electroluminescent materials include hole injection materials, hole transport materials, hole auxiliary materials, light emitting auxiliary materials, electron blocking materials, light emitting materials, electron buffering materials, hole blocking materials, electron transporting materials or electron injection. It can be a material.

The organic electroluminescent material of the present disclosure may comprise at least one compound represented by Formula 1. The compound represented by the formula 1 may be contained in the light emitting layer and / or the electron transporting layer, but is not limited thereto. When included in the light emitting layer, the compound of formula 1 may be included as a host, and when included in the electron transport layer, the compound of formula 1 may be included as an electron transport material.

In the following, the compounds represented by Formula 1 are described in detail.

The compound of formula 1 has the following formulas 2-8:

(During the ceremony,
X _{1 to} X ₃ , Ar ₁ , Ar ₂ and R _{1 to} R ₃ are as defined in Equation 1).
Can be represented by any one of.

In Equation 1 above, X _{1 to} X ₃ each independently represent _{N or CR 3} provided that at least one of them is N. Preferably, at least two of _{X 1 to} X _{3 are N.}

L ₁ represents a substituted or unsubstituted arylene having 10 carbon atoms, preferably a substituted or unsubstituted naphthylene, and more preferably an unsubstituted naphthylene.

Ar ₁ , Ar ₂ and R _{1 to} R ₃ are independently hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted, respectively. Alternatively, unsubstituted (3 to 30-membered ring) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted. Alternatively, unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted. Alternatively, an unsubstituted mono- or di- (C1-C30) alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) arylamino or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylami. Represented; or coupled with an adjacent substituent, substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic ring, aromatic ring or a combination thereof, wherein the carbon atom is nitrogen. , A substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic ring, aromatic ring or a combination thereof, which can be replaced with at least one heteroatom selected from oxygen and sulfur.

Further, Ar ₁ and Ar ₂ preferably independently represent substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-20-membered ring) heteroaryl, and more preferably independently of each other. Represents an unsubstituted or (C1-C30) alkyl substituted (C6-C25) aryl or unsubstituted (5-20-membered ring) heteroaryl.

Further, R _{1 to} R ₃ preferably independently represent hydrogen, substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5-20-membered ring) heteroaryl, and more preferably. Each independently represents hydrogen, unsubstituted (C6-C20) aryl or unsubstituted (5-20-membered ring) heteroaryl.

According to one embodiment of the present disclosure, in Equation 1 above, X _{1 to} X _{3 each independently represent N or CR 3} provided that at least two of them are N; L ₁ is. , Representing substituted or unsubstituted naphthylene; Ar ₁ and Ar ₂ independently represent substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-20-membered ring) heteroaryl; R ₁ ~ R ₃ independently represent hydrogen, substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5-20-membered ring) heteroaryl, respectively.

According to another embodiment of the present disclosure, in Equation 1 above, X _{1 to} X _{3 each independently represent N or CR 3} provided that at least two of them are N; L ₁ Represents unsubstituted naphthylene; Ar ₁ and Ar ₂ are independently unsubstituted or substituted with (C1-C30) alkyl (C6-C25) aryl or unsubstituted (5-20-membered ring) hetero. Represents aryl; R _{1 to} R ₃ independently represent hydrogen, unsubstituted (C6-C20) aryl or unsubstituted (5-20-membered ring) heteroaryl, respectively.

As used herein, "(C1-C30) alkyl" has 1 to 30 carbon atoms constituting the chain, preferably having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. It is intended to be linear or branched alkyl and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. The "(C2-C30) alkenyl" is a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, preferably having 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Intended to be, it comprises vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. "(C2-C30) alkynyl" is a linear or branched alkynyl having 2 to 30 carbon atoms constituting a chain, preferably having 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. It is intended to be ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. "(C3-C30) cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 rings of backbone carbon atoms, preferably having 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., with the intention of being. The "(3-7 membered ring) heterocycloalkyl" is selected from the group consisting of B, N, O, S, Si and P, preferably at least one selected from the group consisting of O, S and N. It is intended to be a cycloalkyl having a heteroatom and a backbone atom of 3 to 7 rings, preferably a backbone atom of 5 to 7 rings, and contains tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. "(C6-C30) aryl (len)" is an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, preferably 6 to 25 ring backbone carbon atoms, more preferably 6 to 18 ring backbone carbon atoms. Intended to be a monocyclic or fused ring radical derived from hydrogen and capable of being partially saturated, it contains a spiro structure and contains phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl. , Phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, perylenyl, chrysenyl, naphthalsenyl, fluoranthenyl, Includes spirobifluorenyl and the like. A "(3-30-membered ring) heteroaryl (en)" is at least one selected from the group consisting of B, N, O, S, Si and P, preferably 1 to 4 heteroatoms and 3 to 3 to. Intended to be an aryl group with 30 backbone atoms, it is a monocyclic ring or a fused ring fused with at least one benzene ring, which can be partially saturated and at least one. It can be formed by attaching a heteroaryl or an aryl group to a heteroaryl group by a single bond, contains a spiro structure, and contains frills, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isooxazolyl, oxazolyl. , Oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, frazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, etc. , Benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindrill, indrill, benzoindrill, indazolyl, benzothiasiazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl , Bentoquinoxalinyl, naphthyldinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxadinyl, phenothiadinyl, phenanthridinyl, benzodioxolyl, dihydroacryldinyl, etc. include. "Halogen" includes F, Cl, Br and I.

As used herein, the term "substituent" in the expression "substituent or unsubstituted" means that a hydrogen atom in one functional group has been replaced by another atom or functional group, i.e., a substituent. Substituted arylene with 10 carbon atoms in L ₁ , Ar ₁ , Ar ₂ and R _{1 to} R ₃ , substituted (C1-C30) alkyl, substituted (C6-C30) aryl (len), substituted (3 to 30). Memberd Ring) Heteroaryl, Substituent (C3-C30) Cycloalkyl, Substituent (C1-C30) alkoxy, Substituent Tri (C1-C30) Alkylsilyl, Substituent Di (C1-C30) Alkyl (C6-C30) Arylsilyl, Substituent (C1-C30) Alkyldi (C6-C30) arylsilyl, substituted tri (C6-C30) arylsilyl, substituted mono- or di- (C1-C30) alkylamino, substituted mono- or di- (C6-C30) aryl Substituents of amino, substituted (C1-C30) alkyl (C6-C30) arylamino and substituted monocyclic or polycyclic (C3-C30) alicyclic rings, aromatic rings or combinations thereof are independent of each other. , Heavy hydrogen; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) Alkylthio; (C3-C30) Cycloalkyl; (C3-C30) Cycloalkenyl; (3-7-membered ring) Heterocycloalkyl; (C6-C30) Aryloxy; (C6-C30) Arylthio; Non (5-30-membered ring) heteroaryl substituted or substituted with (C6-C30) aryl; (C6-C30) aryl substituted with unsubstituted or (5-30-membered ring) heteroaryl; tri (C1-C30) ) Alkylsilyl, tri (C6-C30) arylsilyl; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; amino; mono- or di-( C1-C30) alkylamino; unsubstituted or (C1-C30) alkyl-substituted mono- or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) C30) Alkylcarbonyl; (C1-C30) Arylcarbonyl; (C6-C30) Arylcarbonyl; Di (C6-C30) Arylboronyl ; Di (C1-C30) Alkylboronyl ; (C1-C30) Alkyl (C6-C30) Arylboronyl ; (C6-C30) aryl (C1-C30) alkyl; and And at least one selected from the group consisting of (C1-C30) alkyl (C6-C30) aryl, preferably each independently (C1-C6) alkyl.

The compound represented by the formula 1 is the following compound:

, But not limited to them.

The compound of formula 1 according to the present disclosure can be prepared by a synthetic method known to those skilled in the art. For example, it can be prepared according to the following reaction scheme.

In the formula, X _1- X ₃ , L ₁ , Ar ₁ , Ar ₂ , R ₁ , R ₂ , a and b are as defined in formula 1, and OTf represents trifluoromethanesulfonate.

The present disclosure provides an organic electroluminescent material comprising an organic electroluminescent compound of formula 1 and an organic electroluminescent device comprising this material.

The above material can consist of an organic electroluminescent compound according to the present disclosure alone, or can further comprise conventional materials commonly used for organic electroluminescent materials.

The organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. The organic layer may contain at least one organic electroluminescent compound of formula 1.

One of the first and second electrodes can be the anode and the other can be the cathode. The organic layer may include a light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer and electrons. It may further include at least one layer selected from the blocking layers.

The organic electroluminescent compound of the formula 1 of the present disclosure includes a light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, and an intermediate layer. It may be included in one or more layers of a hole blocking layer and an electron blocking layer, preferably one or more layers of a light emitting layer and an electron transporting layer. When used in a light emitting layer, the organic electroluminescent compound of formula 1 of the present disclosure can be included as a host material. Preferably, the light emitting layer can further contain one or more dopants. If desired, the organic electroluminescent compounds of the present disclosure can be used as co-host materials. That is, the light emitting layer can further contain a compound other than the organic electroluminescent compound (first host material) of the formula 1 of the present disclosure as the second host material. In the present specification, the weight ratio of the first host material to the second host material is in the range of 1:99 to 99: 1.

The second host material can be any known host. The following formulas 11 to 17
H- (Cz-L ₄ ) _h- M -------- (11)
H- (Cz) _i- L _4- M -------- (12)

(During the ceremony,
Cz has the following structure:

Represents;
A represents -O- or -S-;
R _{21 to} R ₂₄ are independently hydrogen, dehydrogen, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members). Ring) Heteroaryl or -SiR ₂₅ R ₂₆ R ₂₇ (where R _25- R ₂₇ are each independently substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl. It represents represents); _{L 4} is a single bond, a substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (5-30 membered ring) heteroarylene; M is a substituted or unsubstituted (C6-C30 ) Aryl or substituted or unsubstituted (5-30-membered ring) heteroaryl; Y ₁ and Y ₂ are independent of each other, provided that Y ₁ and Y ₂ are not present at the same time, -O-, -S. Represents −, −N (R ₃₁ ) − or −C (R ₃₂ ) (R ₃₃ ) −; R _{31 to} R ₃₃ are independently substituted or unsubstituted (C1-C30) alkyl, substituted or non-substituted, respectively. Represents a substituted (C6-C30) aryl or a substituted or unsubstituted (5-30-membered ring) heteroaryl; R ₃₂ and R ₃₃ may be the same or different; h and i are 1 independently of each other. Represents an integer of ~ 3; j, k, l and m each independently represent an integer of 1 to 4; q represents an integer of 1 to 3; h, i, j, k, l, If m or q represents an integer greater than or equal to 2, each (Cz-L ₄ ), each (Cz), each R ₂₁ , each R ₂₂ , each R ₂₃ or each R ₂₄ may be the same or different;
Y _{3 to Y 5} independently _{represent CR 34} or N;
R ₃₄ represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered ring) heteroaryl;
B ₁ and B ₂ independently represent hydrogen, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered ring) heteroaryl;
B ₃ represents substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered ring) heteroaryl;
L ₅ represents a single bond, substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (5-30 membered ring) heteroarylene;
Ar _{31 to} Ar ₃₃ each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3 to 30-membered ring) heteroaryl; or combined with an adjacent substituent. Forming substituted or unsubstituted monocyclic or polycyclic (3-30 membered) alicyclic rings, aromatic rings or combinations thereof; and L ₃₁ are single bound, substituted or unsubstituted (C6-C30). Aromatic or substituted or unsubstituted (3 to 30-membered ring) representing a heteroarylene)
A host selected from the group consisting of the compounds of the above may be preferred.

In equation 17,
Ar _{31 to} Ar ₃₃ preferably independently represent substituted or unsubstituted (C6-C25) aryls or substituted or unsubstituted (5-25 membered ring) heteroaryls, respectively. Specifically, Ar _{31 to} Ar ₃₃ are preferably independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzoflu. Olenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted indolocarba Zoryl, substituted or unsubstituted indenocarbazolyl, substituted or unsubstituted benzothienocarbazolyl, substituted or unsubstituted benzoflocarbazolyl, substituted or unsubstituted benzoindrocarbazolyl, substituted or unsubstituted dibenzoindro It may represent, but is not limited to, carbazolyl, substituted or unsubstituted phenanthrooxazolyl, substituted or unsubstituted phenanthrothiazolyl, and the like.

L ₃₁ preferably represents a single-bonded, substituted or unsubstituted (C6-C25) arylene or substituted or unsubstituted (5-20-membered ring) heteroarylene, and more preferably single-bonded, substituted or unsubstituted (C6-C6-). C20) Represents an arylene or an unsubstituted (5-15 membered ring) heteroarylene. Specifically, L ₃₁ is a single-bonded, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted benzofluorenylene, substituted or unsubstituted ter. It may represent, but is not limited to, phenylene, substituted or unsubstituted naphthylphenylene, substituted or unsubstituted phenylnaphthylene, and the like.

Specifically, an example of the second host material is as follows.

(In the formula, TPS represents a triphenylsilyl group)
However, it is not limited to them.

The dopant contained in the organic electroluminescent device according to the present disclosure may preferably be at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure is not particularly limited, but may be selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt). , Preferably may be selected from ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably ortho-metallized iridium complex.

The dopants contained in the organic electroluminescent devices of the present disclosure can be selected from, but not limited to, the group consisting of compounds represented by the following formulas 101-104.

In the formula, L has the following structure:

(R ₁₀₀ , R ₁₃₄ and R ₁₃₅ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C3-C30) cycloalkyl;
R _{101 to} R ₁₀₉ and R _{111 to} R ₁₂₃ are independently hydrogen, dehydrogen, halogen, unsubstituted or substituted with heavy hydrogen or halogen (C1-C30) alkyl, substituted or unsubstituted (C3-), respectively. C30) Represents cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano or substituted or unsubstituted (C1-C30) alkoxy; _{adjacent substituents of R 106-} R ₁₀₉ are bonded to each other and substituted or substituted. Unsubstituted fused rings can be formed, such as unsubstituted or alkyl substituted fluorene, unsubstituted or alkyl substituted dibenzothiophene or unsubstituted or alkyl substituted dibenzofuran; flanking _{R 120-} R _123. The groups may be attached to each other to form a substituted or unsubstituted fused ring, eg, a quinoline substituted or substituted with at least one of alkyl, aryl, aralkyl and alkylaryl;
R _{124 to} R ₁₃₃ and R _{136 to} R ₁₃₉ independently represent hydrogen, dehydrogen, halogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl, respectively; R. _{Adjacent substituents of 124-} R ₁₂₇ are bonded to each other and are substituted or unsubstituted fused rings, such as unsubstituted or alkyl substituted fluorene, unsubstituted or alkyl substituted dibenzothiophene or unsubstituted or alkyl. Can form dibenzofurans substituted with;
X represents CR ₅₁ R ₅₂ , O or S;
R ₅₁ and R ₅₂ independently represent substituted or unsubstituted (C1-C10) alkyl or substituted or unsubstituted (C6-C30) aryl;
R _{201 to} R ₂₁₁ are independently hydrogen, dehydrogen, halogen, unsubstituted or substituted with dehydrogen or halogen (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl or non-substituted, respectively. Represents a substituted or alkyl or demultiplexed (C6-C30) aryl; _{adjacent substituents on R 208-} R ₂₁₁ are attached to each other with a substituted or unsubstituted fused ring, eg, unsubstituted or alkyl. It may form substituted fluorene, unsubstituted or alkyl substituted dibenzothiophene or unsubstituted or alkyl substituted dibenzofuran;
f and g each independently represent an integer of 1-3; where f or g is an integer greater than or equal to 2, each R ₁₀₀ may be the same or different; and s may be. Represents an integer from 1 to 3)
Is selected from.

Specifically, examples of dopant compounds are as follows:

However, it is not limited to them.

The organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode.

One of the first and second electrodes can be the anode and the other can be the cathode. The organic layer may include a light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer and electrons. It may further include at least one layer selected from the blocking layers.

The organic layer may further comprise at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds.

In addition, in the organic electroluminescent device according to the present disclosure, the organic layer is a metal of Group 1 of the periodic table, a metal of Group 2, a transition metal of the 4th period, a transition metal of the 5th period, a lanthanide and a d-transition element. It may further comprise at least one metal selected from the group consisting of organic metals or at least one complex compound comprising said metal.

In addition, the organic electroluminescent device according to the present disclosure is at least one luminescent compound comprising, in addition to the compounds according to the present disclosure, a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the art. By further including a layer, white light can be emitted. Also, if desired, the device may further include a yellow or orange light emitting layer.

In the organic electroluminescent device according to the present disclosure, at least one layer (hereinafter referred to as "surface layer") is preferably placed on the inner surface of one or both electrodes, a chalcogenide layer, a metal halide layer and metal oxidation. Selected from the material layer. Specifically, a chalcogenide (such as an oxide) layer of silicon or aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and the metal halide or metal oxide layer is preferably electroluminene. It is placed on the cathode surface of the cent medium layer. Such a surface layer provides operational stability for organic electroluminescent devices. Preferably, the chalcogenide comprises SiO _X (1 ≦ X ≦ 2), AlO _X (1 ≦ X ≦ 1.5), SiON, SiAlON and the like; the metal halide is LiF, MgF ₂ , CaF ₂ , etc. Includes rare earth metal fluorides and the like; the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

A hole injection layer, a hole transport layer, an electron blocking layer or a combination thereof can be used between the anode and the light emitting layer. The hole injection layer can be multi-layered to lower the hole-injection barrier (or hole-injection voltage) from the anode to the hole-transporting layer or electron-blocking layer, where each of the multi-layers contains two compounds. Can be used at the same time. The hole transport layer or electron blocking layer can also be multi-layered.

An electron buffering layer, a hole blocking layer, an electron transporting layer, an electron injecting layer or a combination thereof can be used between the light emitting layer and the cathode. The electron buffer layer can be multi-layered to control the injection of electrons and improve the interfacial properties between the light emitting layer and the electron-injected layer, where each of the multi-layers uses two compounds simultaneously. obtain. The hole blocking layer or the electron transporting layer can also be multi-layered, where each of the multi-layered can use multiple compounds.

The light emitting auxiliary layer may be placed between the anode and the light emitting layer or between the cathode and the light emitting layer. If a light emitting auxiliary layer is placed between the anode and the light emitting layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. If a light emitting auxiliary layer is placed between the cathode and the light emitting layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole overflow. Also, the hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light emitting layer, and is effective for promoting or blocking the hole transport rate (or hole injection rate). It is possible, which allows the charge balance to be controlled. In addition, an electron blocking layer can be placed between the hole transporting layer (or hole injecting layer) and the light emitting layer to prevent the overflow of electrons from the light emitting layer and prevent light emission leakage, thereby emitting excitons. Can be confined in the layer. When an organic electroluminescent device comprises two or more hole transport layers, the further included hole transport layers can be used as a hole auxiliary layer or an electron blocking layer. The hole auxiliary layer and the electron blocking layer may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

Preferably, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transporting compound and a reducing dopant or a mixed region of a hole transporting compound and an oxidizing dopant is placed on at least one surface of a pair of electrodes. obtain. In this case, the electron transporting compound is reduced to an anion, thus making it easier to inject and transport electrons from the mixed region into the light emitting medium. In addition, the hole-transporting compound is oxidized to cations, thus making it easier to inject and transport holes from the mixed region into the light emitting medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds; the reducing dopant comprises alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof. The reducing dopant layer can be used as a charge generation layer for producing an organic EL device having two or more light emitting layers that emit white light.

In order to form each layer constituting the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum deposition, sputtering, plasma, ion plating method or a wet film forming method such as spin coating, dip coating, and sink coating method. Can be used. When forming a film of the first host compound and the second host compound of the present disclosure, a co-evaporation or a mixed evaporation method is used.

When the wet film forming method is used, a thin film is formed by dissolving or dispersing the materials constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran and dioxane. The solvent is not particularly limited as long as the material constituting each layer can be dissolved or dispersed in a solvent that does not cause any problem in forming the film.

By using the organic electroluminescent devices of the present disclosure, display devices such as smartphones, tablets, notebooks, PCs, TVs or vehicles or lighting fixtures such as indoor or outdoor lighting fixtures can be manufactured.

In the following, the preparation method of the compound of the present disclosure, the physical properties of the compound and the luminescence property of the organic electroluminescent device containing the present compound will be described in detail with respect to the representative compound of the present disclosure. However, the present disclosure is not limited to the following examples.

Example 1: Preparation of compound H-1

10 g of compound 1-1 (46 mmol), 27 g of 2- (4-bromonaphthalene-1-yl) -4- (naphthalen-2-yl) -6-phenyl-1,3,5-triazine (55 mmol) , 1 g of palladium (II) acetate (5 mmol), 3.8 g of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (9 mmol), 6.6 g of sodium tert-butoxide (69 mmol) and 230 mL of o-xylene was introduced into the reaction vessel and the mixture was stirred under reflux for 5 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed on a rotary evaporator. The resulting product was then purified by column chromatography to give 9.3 g of compound H-1 (yield: 32%).

[table]

Example 2: Preparation of compound H-2

10 g of compound 1-1 (46 mmol), 24 g of 2- (4-bromonaphthalene) -4,6-diphenyl-1,3,5-triazine (55 mmol), 1 g of palladium (II) acetate (5 mmol). ), 3.8 g of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (9 mmol), 6.6 g of sodium tert-butoxide (69 mmol) and 230 mL of o-xylene were introduced into the reaction vessel. The mixture was stirred under reflux for 5 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed on a rotary evaporator. The resulting product was then purified by column chromatography to give 8.2 g of compound H-2 (yield: 31%).

[table]

Device Examples 1 and 2: Manufacture of an OLED device using the organic electroluminescent compound according to the present disclosure for an electron transport layer An organic light emitting diode (OLED) device containing the compound of the present disclosure was manufactured. A transparent electrode indium tin oxide (ITO) thin film (10Ω / sq) (Geomatec, Japan) on a glass substrate for an OLED device was sequentially ultrasonically cleaned with acetone and isopropanol and then stored in isopropanol. Next, the ITO substrate was attached to the substrate holder of the vacuum vapor deposition apparatus. Compound HI-1 was introduced into the cell of the vacuum deposition apparatus and then the pressure in the chamber of the apparatus was controlled to ^{10-7 torr.} Then, an electric current was applied to the cell to evaporate the material introduced above, thereby forming a first hole injection layer having a thickness of 60 nm on the ITO substrate. Compound HI-2 is then introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby causing a second hole having a thickness of 5 nm on the first hole injection layer. An injection layer was formed. Compound HT-1 is introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, whereby a first hole transport layer having a thickness of 20 nm on the second hole injection layer. Formed. Compound HT-2 is introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, whereby a second hole transport layer having a thickness of 5 nm on the first hole transport layer. Formed. After forming the hole injection layer and the hole transport layer, the light emitting layer was then vapor-deposited as follows. Compound BH-1 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound BD-1 was introduced into another cell as a dopant. The two materials were evaporated at different ratios and vaporized at a doping amount of 2 wt% based on the total amount of host and dopant to form a light emitting layer with a thickness of 20 nm on the second hole transport layer. Compound H-1 or H-2 and compound EI-1 are then introduced into the other two cells and simultaneously evaporated at a ratio of 1: 1 and evaporated to form electrons having a thickness of 35 nm on the light emitting layer. A transport layer was formed. Next, compound EI-1 is deposited on the electron transport layer as an electron injection layer having a thickness of 2 nm, and then an Al cathode having a thickness of 80 nm is deposited on the electron injection layer by another vacuum vapor deposition apparatus. rice field. In this way, the OLED device was manufactured. All materials used to make OLED devices were purified by vacuum sublimation in ^{10-6 torr.}

The table below shows the drive voltage in one knit when the organic electroluminescent device starts to emit light, and the period for the brightness to decrease from 100% to 90% at the brightness of 2,000 knits of the manufactured OLED device. Provide to 1.

Comparative Examples 1 and 2: Production of OLED device using a conventional organic electroluminescent compound for an electron transport layer In Comparative Examples 1 and 2, the electron transport material of Table 1 was used instead of H-1 or H-2. Except for that, the OLED device was manufactured in the same manner as in Device Examples 1 and 2. The evaluation results of the organic electroluminescent devices of Comparative Examples 1 and 2 are provided in Table 1 below.

Organic electroluminescent devices containing the compounds of the present disclosure retain good drive voltage characteristics similar to organic electroluminescent devices containing conventional compounds and are significantly improved over organic electroluminescent devices containing conventional compounds. Shows the life characteristics.

Device Example 3: Manufacture of an OLED device using the organic electroluminescent compound as a host according to the present disclosure An OLED device was manufactured using the organic electroluminescent compound of the present disclosure. Transparent electrodes on glass substrates for OLED devices Indium tin oxide (ITO) thin films (10Ω / sq) (Geomatec, Japan) are sequentially ultrasonically washed with trichloroethylene, acetone, ethanol and distilled water and stored in isopropanol. bottom. Next, the ITO substrate was attached to the substrate holder of the vacuum vapor deposition apparatus. Compound HI-1 as the first hole injection material was introduced into the cell of the vacuum deposition apparatus and then the pressure in the chamber of the apparatus was controlled to ^{10-6 torr.} Then, an electric current was applied to the cell to evaporate the material introduced above, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Compound HI-2 as the second hole injection material was then introduced into another cell of the vacuum vapor deposition apparatus and vaporized by applying an electric current to the cell, whereby 5 nm on the first hole injection layer. A thick second hole injection layer was formed. The compound HT-1 as the first hole transport material was introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby having a thickness of 10 nm on the second hole injection layer. The first hole transport layer having the above was formed. Compound HT-3 as a second hole transport material is introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby having a thickness of 60 nm on the first hole transport layer. A second hole transport layer having a hole was formed. After forming the hole injection layer and the hole transport layer, the light emitting layer was then vapor-deposited as follows. Compound H-2 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-71 was introduced into another cell as a dopant. The two materials were evaporated at different ratios and vaporized at a doping amount of 3 wt% based on the total amount of host and dopant to form a light emitting layer with a thickness of 40 nm on the second hole transport layer. Compound ET-2 and compound EI-1 are then introduced into the other two cells and simultaneously evaporated at a 1: 1 ratio and vapor-deposited to form an electron transport layer with a thickness of 35 nm on the light emitting layer. bottom. Next, compound EI-1 was deposited as an electron injection layer having a thickness of 2 nm, and then an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus. In this way, the OLED device was manufactured.

As a result, a power efficiency of 22.3 lm / W is shown at 3.1 V, ^{a red light of 1000 cd / m 2} is emitted, and it takes to reduce the brightness from 100% to 95% at 5,000 knits and constant current. The time was 59 hours.

Comparative Example 3: Manufacture of an OLED device using a conventional organic electroluminescent compound as a host The OLED device is used in Device Example 3 except that compound X-1 is used as a host instead of H-2. Manufactured in the same way.

The result shows a power efficiency of 18.7 lm / W at 3.6 V, emits 1000 cd / m ² of red light, and is required to reduce the brightness from 100% to 95% at 5,000 knits and constant current. The time was 31 hours.

Organic electroluminescent devices using the organic electroluminescent compounds of the present disclosure as hosts have a lower drive voltage and are similar or better than organic electroluminescent devices containing conventional organic electroluminescent compounds. It exhibits excellent power efficiency, especially significantly better life characteristics.

Device Examples 4-13: Manufacture of an OLED device using the organic electroluminescent compound according to the present disclosure as one of a plurality of hosts An OLED device was manufactured using the organic electroluminescent compound of the present disclosure. Transparent electrodes on glass substrates for OLED devices Indium tin oxide (ITO) thin films (10Ω / sq) (Geomatec, Japan) were sequentially ultrasonically cleaned with trichloroethylene, acetone, ethanol and distilled water, then in isopropanol. Stored in. Next, the ITO substrate was attached to the substrate holder of the vacuum vapor deposition apparatus. Compound HI-1 as the first hole injection material was introduced into the cell of the vacuum deposition apparatus and then the pressure in the chamber of the apparatus was controlled to ^{10-6 torr.} Then, an electric current was applied to the cell to evaporate the material introduced above, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Compound HI-2 as the second hole injection material was then introduced into another cell of the vacuum vapor deposition apparatus and vaporized by applying an electric current to the cell, whereby 5 nm on the first hole injection layer. A thick second hole injection layer was formed. The compound HT-1 as the first hole transport material was introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby having a thickness of 10 nm on the second hole injection layer. The first hole transport layer having the above was formed. Compound HT-2 as a second hole transport material is introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby having a thickness of 60 nm on the first hole transport layer. A second hole transport layer having a hole was formed. After forming the hole injection layer and the hole transport layer, the light emitting layer was then vapor-deposited as follows. The first host in Table 2 was introduced into one cell of the vacuum vapor deposition apparatus, the second host was introduced into another cell, and compound D-71 was introduced into another cell as a dopant. The first and second hosts are evaporated in a 1: 1 ratio and the dopant is deposited with a doping amount of 3 wt% based on the total amount of host and dopant to a thickness of 40 nm on the second hole transport layer. A light emitting layer having a host was formed. Compound ET-2 and compound EI-1 are then introduced into the other two cells and simultaneously evaporated at a 1: 1 ratio and vapor-deposited to form an electron transport layer with a thickness of 35 nm on the light emitting layer. bottom. Next, compound EI-1 was deposited as an electron injection layer having a thickness of 2 nm, and then an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus. In this way, the OLED device was manufactured.

Table 2 below provides the duration (T95) for the brightness of the manufactured OLED device to decrease from 100% to 95% at a brightness of 5,000 knits and a constant current.

Table 2 shows that organic electroluminescent devices using the organic electroluminescent compounds according to the present disclosure as one of a plurality of hosts exhibit excellent luminous efficiency and lifetime characteristics.

Claims (10)

Equation 1:

(During the ceremony,
X _{1 to} X ₃ each independently represent _{N or CR 3} provided that at least one of them is N;
L ₁ represents a substituted or unsubstituted arylene having 10 carbon atoms;
Ar ₁ , Ar ₂ and R ₃ are independently hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted. (3-30-membered ring) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted. Di (C1-C30) Alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted Represents mono or di (C1-C30) alkylamino, substituted or unsubstituted mono or di (C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or adjacent. Coupled with substituents, substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic rings, aromatic rings or combinations thereof, the carbon atom of which is selected from nitrogen, oxygen and sulfur. Form substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic rings, aromatic rings or combinations thereof that can be replaced by at least one heteroatom.
R ₁ and R ₂ are independently hydrogen, dehydrogen, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to). 30-membered ring) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1) -C30) Alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono or di Represents (C1-C30) alkylamino, substituted or unsubstituted mono or di (C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or with an adjacent substituent. A coupled, substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic ring in which the carbon atom is replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur. The resulting, substituted or unsubstituted monocyclic or polycyclic (C3-C30) alicyclic ring is formed;
The heteroaryl contains at least one heteroatom selected from B, N, O, S, Si and P;
a is an integer of 1 to 4, and b is an integer of 1 to 6;
Where a or b is an integer greater than or _{equal to 2} , and each R ₁ and each R 2 may be the same or different).
An organic electroluminescent compound represented by. The _{substituted arylene having 10 carbon atoms in L 1} , Ar ₁ , Ar ₂ and R _{1 to} R ₃ , the substituted arylene, the substituted (C1-C30) alkyl, the substituted (C6-C30) aryl (len), the substituted. (3-30-membered ring) heteroaryl, said substituted (C3-C30) cycloalkyl, said substituted (C1-C30) alkoxy, said substituted tri (C1-C30) alkylsilyl, said substituted di (C1-C30) alkyl ( C6-C30) arylsilyl, said substituted (C1-C30) alkyldi (C6-C30) arylsilyl, said substituted tri (C6-C30) arylsilyl, said substituted mono or di (C1-C30) alkylamino, said substituted mono. Alternatively, di (C6-C30) arylamino, the substituted (C1-C30) alkyl (C6-C30) arylamino and the substituted monocyclic or polycyclic (C3-C30) alicyclic ring, aromatic ring or theirs. The substituents of the combination are each independently heavy hydrogen; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30). ) Alkinyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered ring) heterocycloalkyl; (C6-C30) aryl Oxy; (C6-C30) arylthio; unsubstituted or substituted with (C6-C30) aryl (5-30 membered ring) heteroaryl; unsubstituted or substituted with (5-30 membered ring) heteroaryl (C6) -C30) aryl; tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) aryl Cyril; amino; mono- or di- (C1-C30) alkylamino; unsubstituted or (C1-C30) alkyl-substituted mono- or di- (C6-C30) arylamino; (C1-C30) alkyl ( C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di (C6-C30) arylboronyl; di (C1-C30) alkylboronyl (C1-C30) Alkyl (C6-C30) Arylboronyl; (C6) The organic electroluminescent compound of claim 1, wherein the organic electroluminescent compound is at least one selected from the group consisting of —C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. Equation 1 is the following equations 2-8:

(During the ceremony,
X _{1 to} X ₃ , Ar ₁ , Ar ₂ and R _{1 to} R ₃ are as defined in claim 1).
The organic electroluminescent compound according to claim 1, represented by any one of the above. X _{1 to} X ₃ each independently represent _{N or CR 3} provided that at least two of them are N;
L ₁ represents substituted or unsubstituted naphthylene;
Ar ₁ and Ar ₂ independently represent substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-20-membered ring) heteroaryl; and R _{1 to} R ₃ are independent, respectively. The organic electroluminescent compound according to claim 1, which represents a hydrogen, substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5-20-membered ring) heteroaryl. X _{1 to} X ₃ each independently represent _{N or CR 3} provided that at least two of them are N;
L ₁ represents unsubstituted naphthalene;
Ar ₁ and Ar ₂ each independently represent an unsubstituted or (C1-C30) alkyl substituted (C6-C25) aryl or an unsubstituted (5-20-membered ring) heteroaryl; and R ₁ to The organic electroluminescent compound according to claim 1, wherein R ₃ independently represents hydrogen, an unsubstituted (C6-C20) aryl or an unsubstituted (5-20-membered ring) heteroaryl.

The organic electroluminescent compound according to claim 1, which is selected from the group consisting of. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1. The organic electroluminescent device according to claim 8, wherein the organic electroluminescent compound is contained in an electron transport layer, a light emitting layer, or both of them. The light emitting layer further contains an organic electroluminescent compound other than the organic electroluminescent compound according to claim 9, and the organic electroluminescent compound further contained is described in the following formulas 11 to 17 :.
H- (Cz-L ₄ ) _h- M -------- (11)
H- (Cz) _i- L _4- M -------- (12)

(During the ceremony,
Cz has the following structure:

Represents;
A represents -O- or -S-;
R _{21 to} R ₂₄ are independently hydrogen, dehydrogen, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members). Ring) Heteroaryl or -SiR ₂₅ R ₂₆ R ₂₇ (where R _25- R ₂₇ are each independently substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl. It represents represents); _{L 4} is a single bond, a substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (5-30 membered ring) heteroarylene; M is a substituted or unsubstituted (C6-C30 ) Aryl or substituted or unsubstituted (5-30-membered ring) heteroaryl; Y ₁ and Y ₂ are independent of each other, provided that Y ₁ and Y ₂ are not present at the same time, -O-, -S. Represents −, −N (R ₃₁ ) − or −C (R ₃₂ ) (R ₃₃ ) −; R _{31 to} R ₃₃ are independently substituted or unsubstituted (C1-C30) alkyl, substituted or non-substituted, respectively. Represents a substituted (C6-C30) aryl or a substituted or unsubstituted (5-30-membered ring) heteroaryl; R ₃₂ and R ₃₃ may be the same or different; h and i are 1 independently of each other. Represents an integer of ~ 3; j, k, l and m each independently represent an integer of 1 to 4; q represents an integer of 1 to 3; h, i, j, k, l, If m or q represents an integer greater than or equal to 2, each (Cz-L ₄ ), each (Cz), each R ₂₁ , each R ₂₂ , each R ₂₃ or each R ₂₄ may be the same or different;
Y _{3 to Y 5} independently _{represent CR 34} or N;
R ₃₄ represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered ring) heteroaryl;
B ₁ and B ₂ independently represent hydrogen, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered ring) heteroaryl;
B ₃ represents substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered ring) heteroaryl;
L ₅ represents a single bond, substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (5-30 membered ring) heteroarylene;
Ar _{31 to} Ar ₃₃ each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3 to 30-membered ring) heteroaryl; or combined with an adjacent substituent. Forming substituted or unsubstituted monocyclic or polycyclic (3-30 membered) alicyclic rings, aromatic rings or combinations thereof; and L ₃₁ are single bound, substituted or unsubstituted (C6-C30). Aromatic or substituted or unsubstituted (3 to 30-membered ring) representing a heteroarylene)
The organic electroluminescent device of claim 9, represented by any one of the above.